1-Hydroxybenzotriazole → HCID 53711615, compound

HRID 1267133Notes

Reaction equation

HRID 1267133 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][N:27]([CH2:30][C:31]([OH:33])=O)[CH2:26][CH2:25]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:36]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:41]=[CH:40][CH:39]=[C:38](NC)[CH:37]=1.C1C=CC2N(O)N=[N:56][C:54]=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCN(CC)CC>[C:36]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:41]=[CH:40][CH:39]=[C:38]([CH2:54][NH:56][C:31]([CH2:30][N:27]2[CH2:26][CH2:25][N:24]([C:21]3[CH:22]=[CH:23][C:18]([NH:17][C:15]([C:10]4[C:9]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:34])([F:1])[F:35])=[CH:4][CH:5]=5)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:16])=[CH:19][CH:20]=3)[CH2:29][CH2:28]2)=[O:33])[CH:37]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18545465HCID 18545465, compoundHCID 18545469HCID 18545469, compound

Product 1

HCID 53711615HCID 53711615, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of (4-{4-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-phenyl}-piperazin-1-yl)-acetic acid (241 mg), biphenyl-3-yl-methylamine (95 mg), HOBt (87 mg), and Et3N (202 mg) in CH2Cl2 (20 mL) was added EDCl (125 mg) and the mixture was stirred at room temperature for 16 hours. The organic solution was then washed with water, with a saturated solution of NaHCO3 and dried over Na2SO4. After filtration and evaporation of the filtrate, the residue was purified by flash chromatography eluting with CH2Cl2/MeOH (97/3) and the solid obtained was recrystallized from EtOH to give the title compound (180 mg) as white crystals.

Workup

  1. washThe organic solution was then washed with water, with a saturated solution of NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and evaporation of the filtrate
  4. customthe residue was purified by flash chromatography
  5. washeluting with CH2Cl2/MeOH (97/3)
  6. customthe solid obtained
  7. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-96fa3fe96bbd41c7be0874ef2d46f00c
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

Loading…